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144625-67-2 | 1H-Indole-3-carboxylic acid, 5-fluoro-2-methoxy-, [1-[2-[(methylsulfonyl)amino]ethyl]-4-piperidinyl]methyl ester
CAS No: 144625-67-2 Catalog No: AG001JVP MDL No:
Product Description
Catalog Number:
AG001JVP
Chemical Name:
1H-Indole-3-carboxylic acid, 5-fluoro-2-methoxy-, [1-[2-[(methylsulfonyl)amino]ethyl]-4-piperidinyl]methyl ester
CAS Number:
144625-67-2
Molecular Formula:
C19H26FN3O5S
Molecular Weight:
427.4902
IUPAC Name:
[1-[2-(methanesulfonamido)ethyl]piperidin-4-yl]methyl 5-fluoro-2-methoxy-1H-indole-3-carboxylate
InChI:
InChI=1S/C19H26FN3O5S/c1-27-18-17(15-11-14(20)3-4-16(15)22-18)19(24)28-12-13-5-8-23(9-6-13)10-7-21-29(2,25)26/h3-4,11,13,21-22H,5-10,12H2,1-2H3
InChI Key:
SSPCCAYAIDNNJX-UHFFFAOYSA-N
SMILES:
COc1[nH]c2c(c1C(=O)OCC1CCN(CC1)CCNS(=O)(=O)C)cc(cc2)F
Properties
Complexity:
651
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
0
Exact Mass:
427.158g/mol
Formal Charge:
0
Heavy Atom Count:
29
Hydrogen Bond Acceptor Count:
8
Hydrogen Bond Donor Count:
2
Isotope Atom Count:
0
Molecular Weight:
427.491g/mol
Monoisotopic Mass:
427.158g/mol
Rotatable Bond Count:
9
Topological Polar Surface Area:
109A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
2.2
Literature
| Title | Journal |
|---|---|
| Dual role of serotonin in the pathogenesis of indomethacin-induced small intestinal ulceration: pro-ulcerogenic action via 5-HT3 receptors and anti-ulcerogenic action via 5-HT4 receptors. | Pharmacological research 20120901 |
| Upregulation of mucosal 5-HT3 receptors is involved in restoration of colonic transit after pelvic nerve transection. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20120501 |
| Synergistic effect of acetylcholinesterase inhibition (donepezil) and 5-HT(4) receptor activation (RS67333) on object recognition in mice. | Behavioural brain research 20120421 |
| Inotropic effects of prokinetic agents with 5-HT(4) receptor agonist actions on human isolated myocardial trabeculae. | Life sciences 20120409 |
| Effect of chronic pain on morphine-induced respiratory depression in mice. | Neuroscience 20110203 |
| A 5-HT(4)-receptor activation-induced neural plasticity enhances in vivo reconstructs of enteric nerve circuit insult. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20100701 |
| 5-HT4 and 5-HT2 receptors antagonistically influence gap junctional coupling between rat auricular myocytes. | Journal of molecular and cellular cardiology 20100101 |
| Novel antagonists of serotonin-4 receptors: synthesis and biological evaluation of pyrrolothienopyrazines. | Bioorganic & medicinal chemistry 20090315 |
| Endogenous ghrelin and 5-HT regulate interdigestive gastrointestinal contractions in conscious rats. | American journal of physiology. Gastrointestinal and liver physiology 20080801 |
| Contribution of active and inactive states of the human 5-HT4d receptor to the functional activities of 5-HT4-receptor agonists. | Journal of pharmacological sciences 20080701 |
| Serotonin increases L-type Ca2+ current and SR Ca2+ content through 5-HT4 receptors in failing rat ventricular cardiomyocytes. | American journal of physiology. Heart and circulatory physiology 20071001 |
| 5-HT4 receptor agonists increase sAPPalpha levels in the cortex and hippocampus of male C57BL/6j mice. | British journal of pharmacology 20070401 |
| Comparison of 5-HT4 and 5-HT7 receptor expression and function in the circular muscle of the human colon. | Life sciences 20070306 |
| A 5-HT4 agonist, mosapride, enhances intrinsic rectorectal and rectoanal reflexes after removal of extrinsic nerves in guinea pigs. | American journal of physiology. Gastrointestinal and liver physiology 20050801 |
| Differential functional effects of two 5-HT4 receptor isoforms in adult cardiomyocytes. | Journal of molecular and cellular cardiology 20050801 |
| Prucalopride is a partial agonist through human and porcine atrial 5-HT4 receptors: comparison with recombinant human 5-HT4 splice variants. | Naunyn-Schmiedeberg's archives of pharmacology 20050601 |
| Molecular characterization of a purified 5-HT4 receptor: a structural basis for drug efficacy. | The Journal of biological chemistry 20050527 |
| Frontocortical 5-HT4 receptors exert positive feedback on serotonergic activity: viral transfections, subacute and chronic treatments with 5-HT4 agonists. | Biological psychiatry 20050415 |
| Electrophysiological effects of prucalopride, a novel enterokinetic agent, on isolated atrial myocytes from patients treated with beta-adrenoceptor antagonists. | The Journal of pharmacology and experimental therapeutics 20050401 |
| Appearance of a ventricular 5-HT4 receptor-mediated inotropic response to serotonin in heart failure. | Cardiovascular research 20050301 |
| Effects of the selective serotonin reuptake inhibitor, fluoxetine, on regional gastric contractility. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20050201 |
| New insights into the human 5-HT4 receptor binding site: exploration of a hydrophobic pocket. | British journal of pharmacology 20041001 |
| Serotonergic facilitation of synaptic activity in the developing rat prefrontal cortex. | The Journal of physiology 20040501 |
| Modulation of hippocampal excitability by 5-HT4 receptor agonists persists in a transgenic model of Alzheimer's disease. | Neuroscience 20040101 |
| A 5-HT4 agonist mosapride enhances rectorectal and rectoanal reflexes in guinea pigs. | American journal of physiology. Gastrointestinal and liver physiology 20030801 |
| [3H]GR113808 binding to serotonin 5-HT(4) receptors in the postmortem neocortex of Alzheimer disease: a clinicopathological study. | Journal of neural transmission (Vienna, Austria : 1996) 20030701 |
| 5-HT4 receptors contribute to the motor stimulating effect of levosulpiride in the guinea-pig gastrointestinal tract. | Digestive and liver disease : official journal of the Italian Society of Gastroenterology and the Italian Association for the Study of the Liver 20030401 |
| New benzo[h][1,6]naphthyridine and azepino[3,2-c]quinoline derivatives as selective antagonists of 5-HT4 receptors: binding profile and pharmacological characterization. | Journal of medicinal chemistry 20030102 |
| 5-HT4 receptors exert a frequency-related facilitatory control on dorsal raphé nucleus 5-HT neuronal activity. | The European journal of neuroscience 20020901 |
| Modulation of 5-HT4 receptor function in the rat isolated ileum by fluoxetine: the involvement of endogenous 5-hydroxytryptamine. | British journal of pharmacology 20020501 |
| Central 5-HT(4) receptors and dopamine-dependent motor behaviors: searching for a functional role. | Pharmacology, biochemistry, and behavior 20020401 |
| Characterization of serotonin(4) receptors in adrenocortical aldosterone-producing adenomas: in vivo and in vitro studies. | The Journal of clinical endocrinology and metabolism 20020301 |
| Differences in signal transduction of two 5-HT4 receptor splice variants: compound specificity and dual coupling with Galphas- and Galphai/o-proteins. | Molecular pharmacology 20020101 |
| Enhancement of place and object recognition memory in young adult and old rats by RS 67333, a partial agonist of 5-HT4 receptors. | Neuropharmacology 20011201 |
| The human serotonin 5-HT4 receptor regulates secretion of non-amyloidogenic precursor protein. | The Journal of biological chemistry 20011130 |
| Characterization of the receptors involved in the 5-HT-induced excitation of canine antral longitudinal muscle. | British journal of pharmacology 20011101 |
| Computational model of the complex between GR113808 and the 5-HT4 receptor guided by site-directed mutagenesis and the crystal structure of rhodopsin. | Journal of computer-aided molecular design 20011101 |
| Effects of the enterokinetic prucalopride (R093877) on colonic motility in fasted dogs. | Neurogastroenterology and motility : the official journal of the European Gastrointestinal Motility Society 20011001 |
| Pharmacological characterization of a novel 5-HT4 receptor agonist, TS-951, in vitro. | Pharmacology 20010701 |
| The in vitro pharmacological profile of prucalopride, a novel enterokinetic compound. | European journal of pharmacology 20010629 |
| Effect of the intracerebroventricular administration of GR 113808, a selective 5-HT4 antagonist, on water intake during hyperosmolarity and hypovolemia. | Brazilian journal of medical and biological research = Revista brasileira de pesquisas medicas e biologicas 20010601 |
| 5-HT(4) receptors mediating enhancement of contractility in canine stomach; an in vitro and in vivo study. | British journal of pharmacology 20010401 |
| Neurochemical and electrophysiological evidence that 5-HT4 receptors exert a state-dependent facilitatory control in vivo on nigrostriatal, but not mesoaccumbal, dopaminergic function. | The European journal of neuroscience 20010301 |
| 5HT4(a) and 5-HT4(b) receptors have nearly identical pharmacology and are both expressed in human atrium and ventricle. | Naunyn-Schmiedeberg's archives of pharmacology 20010201 |
| Possible involvement of 5-HT4 receptors, in addition to 5-HT3 receptors, in the emesis induced by high-dose cisplatin in Suncus murinus. | Japanese journal of pharmacology 20010101 |
| Pharmacological characterization of the human 5-HT(4(d)) receptor splice variant stably expressed in Chinese hamster ovary cells. | British journal of pharmacology 20001001 |
| Exploration of the ligand binding site of the human 5-HT(4) receptor by site-directed mutagenesis and molecular modeling. | British journal of pharmacology 20000601 |
| Effect of YNS-15P, a new alpha-2 adrenoceptor antagonist, on stress-stimulated colonic propulsion in rats. | The Journal of pharmacology and experimental therapeutics 19981101 |
| Cloning and expression of a human serotonin 5-HT4 receptor cDNA. | Journal of neurochemistry 19971101 |
| Cloning and expression of human 5-HT4S receptors. Effect of receptor density on their coupling to adenylyl cyclase. | Neuroreport 19971020 |
| Cloning, expression and pharmacology of the mouse 5-HT(4L) receptor. | FEBS letters 19961125 |
| [3H]5-hydroxytryptamine labels the agonist high affinity state of the cloned rat 5-HT4 receptor. | European journal of pharmacology 19960523 |
| 5-Hydroxytryptamine (5-HT)4 receptors in post mortem human brain tissue: distribution, pharmacology and effects of neurodegenerative diseases. | British journal of pharmacology 19950301 |
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